Synthesis via oxazolines. VII. Asymmetric reduction of ketones with chiral hydride reagents

✍ Scribed by A.I. Meyers; Peter M. Kendall

• Publisher: Elsevier Science
• Year: 1974
• Tongue: French
• Weight: 197 KB
• Volume: 15
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82482-5

✦ Synopsis

The recent findings that 2-oxazolines are inert to lithium aluminum hydride' and the successful implementation of a chiral non-racemic oxazoline as a reagent in asymmetric synthesis 2s3 have prompted a study involving oxazoline-hydrides as chiral reducing agents. Several chiral nonracemic oxazolines lwere prepared as previously described 2,3 and evaluated with various ketones in order to assess the degree of asymmetric reduction to chiral secondary alcohols 2. The results of this study are presented in Table I. All asymmetric reductions were performed using slightly Ph LiAlH4 Rl R2 b 'cH/